2-Toluidine hydrochloride → 1-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

HRID 704572

반응식

HRID 704572 반응식
Cl[CH2:2][CH2:3][C:4]1[N:5]=[N:6][C:7]2[C:12]([C:13]=1Cl)=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:15].Cl.[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>O1CCOCC1>[CH3:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:17]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([CH3:15])[C:7]=3[N:6]=[N:5][C:4]=2[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 124842-Toluidine hydrochlorideHCID 200727624-Chloro-3-(2-chloroethyl)-8-methylcinnoline

생성물 1

HCID 200727571-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

3-(2-Chloroethyl)-4-chloro-8-methylcinnoline (2.5 g, 0.01mol) and o-toluidine hydrochloride (1.4 g, 0.01 mol) in 1,4 dioxan (20 ml) were heated under reflux for 20 hours. The solvent was evaporated under reduced pressure to give an oil. The oil was partitioned between chloroform and dilute sodium carbonate solution and extracted further with chloroform (4×100 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated to give an oil. The oil was purified by column chromatography using dichloromethane then chloroform as eluant. The solid obtained was recrystallized from diethyl ether/ dichloromethane to give the title compound, 0.6 g, m.p. 135-137°.

후처리

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customto give an oil
  4. customThe oil was partitioned between chloroform and dilute sodium carbonate solution
  5. extractionextracted further with chloroform (4×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give an oil
  10. customThe oil was purified by column chromatography
  11. customThe solid obtained
  12. customwas recrystallized from diethyl ether/ dichloromethane

출처 및 근거

ORD 기록
ord-7a2061e706aa463688322487297d07ec
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04988695

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